Family-friendly holiday rentals in Searsport

Gothic Victorian Carriage House Apartment

This newly renovated carriage house was the original hayloft of the Gilkey House, a historic American Gothic Victorian built in 1879 by the renowned architect George Harding. Unique, private & luxurious, this 2 bdrm apartment is filled with designer touches. Bright & spacious living area is perfect for families & friends to gather, cook & create memories that will last a lifetime. Walk to the best restaurants and shops, the Farmer's Market, Oceanfront Harbor, trails, Front St. Shipyard & Marina.

Family · Indoor spaces · Parks

Cozy Cottage on the Penobscot – Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Kitchen · Family · Condition

Private Beach, Bar Harbor, Acadia, 15 beds, Pets

" Memories that will last a lifetime". Discover The Retreat House, a charming Waterfront Maine haven near Bar Harbor and Acadia. Unlike typical rentals, our property offers a private beach and stunning water views while being pet-friendly. The House is designed to meet the needs of multi-generational families and larger groups, providing ample space for unforgettable vacation moments. Enjoy beach bonfires, whale watching, lobster bakes, and swimming. Be sure to view the 200+ photos, then book.

Kitchen · Indoor spaces · Amenities

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

Kitchen · Family · Barbecue

Private oceanfront cottage- Steps to Penobscot Bay

Coastal, light and airy- this recently renovated cottage/ guest house is perfect for those seeking to explore all that Midcoast Maine has to offer. Each room offers panoramic views of spectacular Penobscot Bay. Watch for sailboats, eagles, seals and other wildlife from the deck, the Adirondack chairs, or from inside the home. Property is uniquely situated at the head of Penobscot Bay and offers stunning views of sunrise and sunset. Great amenities & comfort for guests. Perfect for couples.

Family · Indoor spaces · Heating

Quiet cottage on the bay

Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Kitchen · Family · Backyard

Historic Stephenson Farm on 35 acre Mason Pond

This water front historic Stephenson Farmhouse is a cozy 3 bedroom farmhouse that sits on 5 acres with frontage on Lower Mason Pond. A bird lovers paradise along with sightings of beaver & river otters. Trail from house leads to waterfront, canoes, paddles & PFD’s and a picnic table. We’ve maintained the antiquity of the house along with many antique pieces of furniture. Enjoy amazing sunsets, expand your birding life list, pick apples and blueberries in season. . . on a nature preserve.

Kitchen · Indoor spaces · Pets

Acadia Region New Oceanfront Cottage

Relax and unwind at this unique waterfront retreat where you can enjoy breathtaking views of the ever-changing tides. Keep an eye out for bald eagles, osprey, and the occasional seal as you soak in the natural beauty around you. This renovated former boathouse combines comfort with convenience, offering the perfect base for your coastal adventures. Situated in Mid Coast, Maine, it's ideally located just an hour from Acadia National Park, 15 minutes from Belfast, and 45 minutes from Camden.

Kitchen · Family · Outdoor spaces

Belfast Harbor Loft | Downtown

Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Kitchen · Indoor spaces · Long stay

Forest Cabin w/ Stunning Wall of Windows

Welcome to Nadair Maine, a 30-acre forest sanctuary. Nestled here is Sunrise Cabin—a peaceful 850 sq ft retreat for 6 where simplicity & beauty live side by side. A wall of windows frames the forest in every season — from snow-dusted pines in winter to the brilliant colors of fall. Fully equipped, cook in the full kitchen, unwind on the porch, or cozy up by the wood stove. Enjoy the fire pit under the stars, or a short drive to coastal adventures. Book your serene Maine escape today!

Family · Indoor spaces · Air conditioning

Streamside Cabin at Trailhead

Enjoy some peace and quiet at this stream side cabin. This stylish little cabin is tucked away at the end of a quiet, dead end road. It is also located just steps away from historic Mount Waldo. Hike up the mountain to see beautiful vistas and a granite quarry. Put in a canoe or kayak at the public boat launch right down the road! Centrally located for travel to many coastal towns and beaches. Right off from scenic Route 1A. One hour away from Acadia National Park.

Indoor spaces · Kitchen · Quiet

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Indoor spaces · Kitchen · Beach